Oxamic Acid → N-[2-(3-Cyclopentyloxy-4-methoxyphenyl)ethyl]oxamide

HRID 275490

Reaktionsgleichung

Reaktionsgleichung von HRID 275490
[C:1]([OH:6])(=O)[C:2]([NH2:4])=[O:3].CN1CCOCC1.ClC(OCC)=O.[CH:20]1([O:25][C:26]2[CH:27]=[C:28]([CH2:34][CH2:35][NH2:36])[CH:29]=[CH:30][C:31]=2[O:32][CH3:33])[CH2:24][CH2:23][CH2:22][CH2:21]1.[Cl-].[NH4+]>COCCOC>[CH:20]1([O:25][C:26]2[CH:27]=[C:28]([CH2:34][CH2:35][NH:36][C:1]([C:2]([NH2:4])=[O:3])=[O:6])[CH:29]=[CH:30][C:31]=2[O:32][CH3:33])[CH2:21][CH2:22][CH2:23][CH2:24]1

Komponenten

7

Edukt 5

HCID 974Oxamic AcidHCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 112763943-Cyclopentyloxy-4-methoxyphenethylamine

Produkt 1

HCID 9861348N-[2-(3-Cyclopentyloxy-4-methoxyphenyl)ethyl]oxamideAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of oxamic acid (1.76 g, 20 mmol) in 1,2-dimethoxyethane (75 mL) under an argon atmosphere was added dropwise N-methylmorpholine (2.55 mL, 23 mmol) followed by ethyl chloroformate (2.20 mL, 23 mmol). After stirring for 1 h at room temperature, a solution of 2-(3-cyclopentyloxy-4-methoxy-phenyl)ethylamine (4.65 g, 20 mmol) in 1,2-dimethoxyethane (30 mL) was added over 5 min, and the resulting mixture was stirred for 2 h. Saturated aqueous ammonium chloride was added and the solvent was removed under reduced pressure. The solid residue was dissolved in methanol/methylene chloride, washed successively with water, 10% hydrochloric acid, aqueous sodium bicarbonate and water and dried (potassium carbonate). The solvent was removed in vacuo and the residue was purified by flash chromatography, eluting with 1% i-propanol/methylene chloride to provide the oxamide (1.82 g, 30%): m.p. 175°-175.5° C.

Aufarbeitung

  1. stirringthe resulting mixture was stirred for 2 h
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe solid residue was dissolved in methanol/methylene chloride
  4. washwashed successively with water, 10% hydrochloric acid, aqueous sodium bicarbonate and water
  5. dry with materialdried (potassium carbonate)
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography
  8. washeluting with 1% i-propanol/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-11799f87b34444998fe8615eefb7b91c
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05393788

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